US2757119A - Bis-(2-chloroethyl) chlorofumarate, fungicidal composition of said compound and method of applying same - Google Patents
Bis-(2-chloroethyl) chlorofumarate, fungicidal composition of said compound and method of applying same Download PDFInfo
- Publication number
- US2757119A US2757119A US391714A US39171453A US2757119A US 2757119 A US2757119 A US 2757119A US 391714 A US391714 A US 391714A US 39171453 A US39171453 A US 39171453A US 2757119 A US2757119 A US 2757119A
- Authority
- US
- United States
- Prior art keywords
- chlorofumarate
- bis
- chloroethyl
- plants
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- XUQCASQMCKGRHJ-WAYWQWQTSA-N bis(2-chloroethyl) (z)-2-chlorobut-2-enedioate Chemical compound ClCCOC(=O)\C=C(/Cl)C(=O)OCCCl XUQCASQMCKGRHJ-WAYWQWQTSA-N 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title claims description 9
- 230000000855 fungicidal effect Effects 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 title description 7
- 238000000034 method Methods 0.000 title description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 description 24
- ZQHJVIHCDHJVII-UPHRSURJSA-N (z)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(/Cl)C(O)=O ZQHJVIHCDHJVII-UPHRSURJSA-N 0.000 description 16
- 239000000417 fungicide Substances 0.000 description 9
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 6
- -1 chlorofumaryl bromide Chemical compound 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000012010 growth Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000221535 Pucciniales Species 0.000 description 3
- 206010037888 Rash pustular Diseases 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 208000029561 pustule Diseases 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFPNBTOAWCBYMT-UPHRSURJSA-N (z)-2-chlorobut-2-enedioyl dichloride Chemical compound ClC(=O)\C=C(/Cl)C(Cl)=O RFPNBTOAWCBYMT-UPHRSURJSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OJAGSSSUBJOESZ-UHFFFAOYSA-N C(CCCCCCCCCCC)OC(C(=C/C(=O)OCCCCCCCCCCCC)Cl)=O Chemical compound C(CCCCCCCCCCC)OC(C(=C/C(=O)OCCCCCCCCCCCC)Cl)=O OJAGSSSUBJOESZ-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000540505 Puccinia dispersa f. sp. tritici Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VYXGXXYXSAMWBM-ARJAWSKDSA-N dimethyl (z)-2-chlorobut-2-enedioate Chemical compound COC(=O)\C=C(/Cl)C(=O)OC VYXGXXYXSAMWBM-ARJAWSKDSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/657—Maleic acid esters; Fumaric acid esters; Halomaleic acid esters; Halofumaric acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
Definitions
- the present invention relates tochlorine-containing dicarboxylates and more particularly provides bis-(2- chloroethyl). chlorofumarate as a new compound, fungicidal compositions: comprising the new compound and methods of inhibiting or entirely preventing fungus growth in which such compositions are used.
- bis-(Z-chloroethyl) chlorofumarate may be easily prepared by contacting ethylene chlorohydrin with a compound selected from the class consisting of chlorofumaric acid or a diacyl halide thereof. Formation of the bis-(Z-chloroethyl) chlorofumarate is particularly easily effected by simply adding the chlorohydrin to a diacyl halide of a halofumaric acid at ordinary room temperatures, the reaction with the halide proceeding according to the scheme:
- diacyl halides When working with the diacyl halides it may be ad vantageous to employ an alkaline material as catalyst although the reaction proceeds with formation of the present ester in very good yields even in the absence of such a catalyst. In some instances, particularly when operating with the acyl halide, operation at diminished pressure is advisable.
- a dehydrating agent is advantageously employed when chlorofumaric acid is used.
- diacyl halides there may be used either chlorofumaryl chloride, chlorofumaryl bromide or chlorofumaryl iodide.
- Bis-(Z-chloroethyl) chlorofumarate is a stable, wellcharacterized compound which may be used for a number of industrial and agricultural purposes. We have found it to be particularly useful as the elfective ingredient in compositions adapted to the treatment of plants and other organic materials which are subject to attack by fungi.
- the present ester is highly efiicient in preventing and retarding fungus growth on plants, fruits, seeds, soils, leather, cotton, Wood and organic materials in general. It may be applied directly to the organic material which is to be treated, but because the bis-(2- chloroethyl) chlorofumarate is effective in extremely dilute concentrations it is preferred to incorporate it with a carrier or diluent.
- Fungicidal dusts may be prepared by mixing the present ester with dusting materials such as talc, clay, lime, bentonite, pumice, fullers earth, etc.
- Dusting materials such as talc, clay, lime, bentonite, pumice, fullers earth, etc.
- Bis-(2-chloroethyl) chlorofumarate is soluble in the usual organic solvents and may be used in solution, e. g., in benzene or kerosene solution as a fungicidal spray.
- Suspensions or oil-in-water emulsions are advantageously employed in the treatment of plants, textiles, leather and other materials with which it is not desirable to employ either a solid carrier or an organic solvent.
- Fungicidal compositions comprising the present active ingredient may be applied only to the surface of the material to be treated as when treating foliage, furs, leather and other comparatively pregnable materials when fungus growth is. to be' prevented or retarded.
- the bis-(2-chloroethyl) chlorofumarate preferably, incorporated with a solid carrier, may be mixed with the seed.
- baths comprising aqueous emulsions of the'fungicide. impregnation of textiles with the fungicides is also advantageously efiec'ted in baths.
- While bis-(Z-chloroethyl) chlorofumarate is'a generally valuable fungicide; it'diifers from the usual organic fungicides and from prior known esters of fumaric or chlorofuma-ric acid inthat it serves as a systemic fungicide and is of significant utility in the treatment of Wheat, beans,xetc. for rustieontrol.
- Application of the fungicide either. to'the plants or to soils in which such plants are growing prevents growth of rust on plants which have been treated with the present fungicide or are supported by soils which have been treated with the fungicide and which normally support the growth of plant life. Growth of rust fungi may also be retarded or prevented by application of the present fungicidal composition to the plant by means of sprays or surface dusts.
- Example 1 To 40.2 g. (0.5 mole) of ethylene chlorohydrin there was gradually dropped 3.74 g. (0.2 mole) of chlorofumaryl chloride over a 10-minute period. The temperature rose to 50 C. After stirring the reaction mixture for an hour, it was distilled to give 44.3 g. theoretical yield) of the substantially pure bis-(2- chloroethyl) chlorofumarate, a white liquid, B. P.
- Example 2 This example describes evaluation of bis-(2-chloroethyl) chlorofumarate as a systemic fungicide against wheat rust.
- the spray consisted of water, containing an 0.25 per cent by weight concentration of the chlorofumarate, and an 0.1 per cent concentration of a commercial surfactant known to the trade as Tween 20" and reputed to be a polyalkylene glycol hexitol anhydride long chain fatty acid partial ester.
- Tween 20 a commercial surfactant known to the trade as Tween 20" and reputed to be a polyalkylene glycol hexitol anhydride long chain fatty acid partial ester.
- a blank spray consisting of only water and 0.1 per cent of the Tween 20 was also employed.
- inoculated plants were sprayed with an atomizer until run-off occurred.
- the plants were then held in the greenhouse until large pustules had developed on control plants, i. e., on inoculated plants which had not been sprayed and on inoculated plants which had been sprayed with the 0.1 per cent aqueous solution of the surfactant in absence of the chlorofumarate.
- a wheat rust fungi-inhibiting composition comprising an inert carrier and bis-(2-chloroethyl) chlorofumarate as the essential active ingredient.
Description
United States Patent 2,757,119 BIS-(Z-CHLORQETHYL) CHLOROFUMARATE,
FUNGTCIDA'L COMPOSITION OF SAID' COM- POUND AND METHOD OF APPLYING SAME George E. Bennett and Arthur H. Schlesinger, Dayton,
Ohio, assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. ApplicationNovember 12, 1953,
SerialNo. 391,714
3 Claims. (Cl. 167-22) The present invention relates tochlorine-containing dicarboxylates and more particularly provides bis-(2- chloroethyl). chlorofumarate as a new compound, fungicidal compositions: comprising the new compound and methods of inhibiting or entirely preventing fungus growth in which such compositions are used.
We have found that bis-(Z-chloroethyl) chlorofumarate may be easily prepared by contacting ethylene chlorohydrin with a compound selected from the class consisting of chlorofumaric acid or a diacyl halide thereof. Formation of the bis-(Z-chloroethyl) chlorofumarate is particularly easily effected by simply adding the chlorohydrin to a diacyl halide of a halofumaric acid at ordinary room temperatures, the reaction with the halide proceeding according to the scheme:
XOOCH g +H0.0HiCHzCl Cl COX OICHzCHzOOCH Cl C O OCHzCHzCl in which X is chlorine, bromine or iodine.
When working with the diacyl halides it may be ad vantageous to employ an alkaline material as catalyst although the reaction proceeds with formation of the present ester in very good yields even in the absence of such a catalyst. In some instances, particularly when operating with the acyl halide, operation at diminished pressure is advisable. A dehydrating agent is advantageously employed when chlorofumaric acid is used. As diacyl halides there may be used either chlorofumaryl chloride, chlorofumaryl bromide or chlorofumaryl iodide.
Bis-(Z-chloroethyl) chlorofumarate is a stable, wellcharacterized compound which may be used for a number of industrial and agricultural purposes. We have found it to be particularly useful as the elfective ingredient in compositions adapted to the treatment of plants and other organic materials which are subject to attack by fungi. The present ester is highly efiicient in preventing and retarding fungus growth on plants, fruits, seeds, soils, leather, cotton, Wood and organic materials in general. It may be applied directly to the organic material which is to be treated, but because the bis-(2- chloroethyl) chlorofumarate is effective in extremely dilute concentrations it is preferred to incorporate it with a carrier or diluent.
Fungicidal dusts may be prepared by mixing the present ester with dusting materials such as talc, clay, lime, bentonite, pumice, fullers earth, etc. Bis-(2-chloroethyl) chlorofumarate is soluble in the usual organic solvents and may be used in solution, e. g., in benzene or kerosene solution as a fungicidal spray. Suspensions or oil-in-water emulsions are advantageously employed in the treatment of plants, textiles, leather and other materials with which it is not desirable to employ either a solid carrier or an organic solvent.
Fungicidal compositions comprising the present active ingredient may be applied only to the surface of the material to be treated as when treating foliage, furs, leather and other comparatively pregnable materials when fungus growth is. to be' prevented or retarded. In other cases, for example, when it is desired to protect seeds from soil micro-organisms harmful to the seeds and plants, the bis-(2-chloroethyl) chlorofumarate preferably, incorporated with a solid carrier, may be mixed with the seed. For protection of fruits, seedlings, plant tubers, etc, it may be advantageous to effect the treatment by employing baths comprising aqueous emulsions of the'fungicide. impregnation of textiles with the fungicides is also advantageously efiec'ted in baths.
While bis-(Z-chloroethyl) chlorofumarate is'a generally valuable fungicide; it'diifers from the usual organic fungicides and from prior known esters of fumaric or chlorofuma-ric acid inthat it serves as a systemic fungicide and is of significant utility in the treatment of Wheat, beans,xetc. for rustieontrol. Application of the fungicide either. to'the plants or to soils in which such plants are growing prevents growth of rust on plants which have been treated with the present fungicide or are supported by soils which have been treated with the fungicide and which normally support the growth of plant life. Growth of rust fungi may also be retarded or prevented by application of the present fungicidal composition to the plant by means of sprays or surface dusts.
The present invention is further illustrated, but not limited, by the following examples:
Example 1 To 40.2 g. (0.5 mole) of ethylene chlorohydrin there was gradually dropped 3.74 g. (0.2 mole) of chlorofumaryl chloride over a 10-minute period. The temperature rose to 50 C. After stirring the reaction mixture for an hour, it was distilled to give 44.3 g. theoretical yield) of the substantially pure bis-(2- chloroethyl) chlorofumarate, a white liquid, B. P.
Example 2 This example describes evaluation of bis-(2-chloroethyl) chlorofumarate as a systemic fungicide against wheat rust.
Seven-day old seedlings of Seneca winter wheat were hand inoculated with wheat leaf rust, Puccinia rubigovera tritici (race 126). The inoculated plants were incubated for 36-40 hours at 68 F. in an illuminated high humidity chamber and then transferred to a greenhouse which was maintained at approximately 72 F. They were allowed to stand in the greenhouse for 72 hours and then treated with a spray containing the bis-(Z-chloroethyl) chlorofumarate of Example 1. The spray consisted of water, containing an 0.25 per cent by weight concentration of the chlorofumarate, and an 0.1 per cent concentration of a commercial surfactant known to the trade as Tween 20" and reputed to be a polyalkylene glycol hexitol anhydride long chain fatty acid partial ester. A blank spray, consisting of only water and 0.1 per cent of the Tween 20 was also employed.
The inoculated plants were sprayed with an atomizer until run-off occurred. The plants were then held in the greenhouse until large pustules had developed on control plants, i. e., on inoculated plants which had not been sprayed and on inoculated plants which had been sprayed with the 0.1 per cent aqueous solution of the surfactant in absence of the chlorofumarate.
At the end of that time observation of the plants was made to determine the degree of rust. The number of infected plants were counted, the roots were examined and the infected plants graded with respect to the number of pustules. Plants which had been treated with the suspension of bis-(2-chloroethyl) chlorofumarate described above were substantially unaffected. The roots of all plants which had been contacted with the bis-(2- chloroethyl) chlorofumarate were in excellent condition. On the other hand inspection of plants which had been treated in the same way with related esters showed widespread infection as follows: At the same concentration, i. e., at the 0.25% concentration, use of bis-(2- ethylhexyl) chlorofumarate, di-n-octylchlorofumarate, di-n-octyl chloromaleate or of didodecyl chloromaleate instead of the bis-(Z-chloroethyl) chlorofumarate in the treating suspension resulted in infection of the plants with development of a large number of pustules on each plant and brown, translucent and rotted roots. Like testing of dimethyl chlorofumarate revealed that this compound was phytotoxic to the seedlings, whereas plants which had been exposed to the bis-(Z-chloroethyl) chlorofumarate remained in healthy condition.
What we claim is:
1. Bis-(Z-chloroethyl) chlorofumarate.
2. A wheat rust fungi-inhibiting composition comprising an inert carrier and bis-(2-chloroethyl) chlorofumarate as the essential active ingredient.
3. The method of protecting wheat plants against rust fungi which comprises contacting said wheat with his- (2-chl0roethyl) chlorofumarate.
References Cited in the file of this patent UNITED STATES PATENTS Searle et al. Oct. 15, 1940 OTHER REFERENCES
Claims (2)
1. BIS-(2-CHLOROETHYL) CHLOROFUMARATE.
2. A WHEAT RUST FUNGI-INHIBITING COMPOSITION COMPRISING AN INERT CARRIER AND BIS-(2-CHLOROETHYL) CHLOROFUMARATE AS THE ESSENTIAL ACTIVE INGREDIENT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US391714A US2757119A (en) | 1953-11-12 | 1953-11-12 | Bis-(2-chloroethyl) chlorofumarate, fungicidal composition of said compound and method of applying same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US391714A US2757119A (en) | 1953-11-12 | 1953-11-12 | Bis-(2-chloroethyl) chlorofumarate, fungicidal composition of said compound and method of applying same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2757119A true US2757119A (en) | 1956-07-31 |
Family
ID=23547649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US391714A Expired - Lifetime US2757119A (en) | 1953-11-12 | 1953-11-12 | Bis-(2-chloroethyl) chlorofumarate, fungicidal composition of said compound and method of applying same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2757119A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2881070A (en) * | 1956-10-10 | 1959-04-07 | Buckman Labor Inc | Processes for the control of slime-forming and other microorganisms and compositionsfor use therefor |
| US2889356A (en) * | 1955-11-29 | 1959-06-02 | Monsanto Chemicals | Conjugated diacetylenic glycol esters |
| US3098003A (en) * | 1961-02-01 | 1963-07-16 | Us Rubber Co | Itaconimide fungicides and algaecides |
| US3098002A (en) * | 1961-02-01 | 1963-07-16 | Us Rubber Co | Method of controlling fungi and algae with nu-phenyl-itaconimides |
| US3138523A (en) * | 1962-04-06 | 1964-06-23 | Us Rubber Co | Method of protecting against arachnids with nu-(3-nitrophenyl) itaconimide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2218181A (en) * | 1939-06-15 | 1940-10-15 | Du Pont | Pest control |
-
1953
- 1953-11-12 US US391714A patent/US2757119A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2218181A (en) * | 1939-06-15 | 1940-10-15 | Du Pont | Pest control |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889356A (en) * | 1955-11-29 | 1959-06-02 | Monsanto Chemicals | Conjugated diacetylenic glycol esters |
| US2881070A (en) * | 1956-10-10 | 1959-04-07 | Buckman Labor Inc | Processes for the control of slime-forming and other microorganisms and compositionsfor use therefor |
| US3098003A (en) * | 1961-02-01 | 1963-07-16 | Us Rubber Co | Itaconimide fungicides and algaecides |
| US3098002A (en) * | 1961-02-01 | 1963-07-16 | Us Rubber Co | Method of controlling fungi and algae with nu-phenyl-itaconimides |
| US3138523A (en) * | 1962-04-06 | 1964-06-23 | Us Rubber Co | Method of protecting against arachnids with nu-(3-nitrophenyl) itaconimide |
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